Pretty, Polite, & Pumped As Hell: How to Rock a First Date

I wore this in 2011 on my first date with the man who would become my first serious boyfriend. Aw, baby Kate.

Oh, first dates. Is there any situation more nervewracking, or more filled with potential?!

I get freaked out every time I go on a first date, even if it’s with someone I’m not especially excited about. I’ve been known to send panicked last-minute texts to friends while putting my outfit together: “What if he thinks I’m ugly or boring?!” “What if he’s a serial killer?!” “What if he wants to do [x sex act] and I’m bad at it?!”

However, once the jitters are sorted out and I’m on my way, I usually have a pretty good time. Whether a first date ends in passionate sex or a chaste cheek-kiss, whether it leads to something more or nothing whatsoever, it’s still an interesting opportunity to get out of your comfort zone and go on an adventure of sorts.

Here are my guiding principles for a successful first date. Of course, you could follow these to a T and still have a disastrously bad time… but at least if you do, it’ll be the other person’s fault and not yours!

1. Be on time. Lateness is the height of rudeness. A first date is like a sexy job interview: your aim should be to put your best foot forward and project the absolute best possible image of yourself. That means being polite and respectful, including in the way you manage your time. It’s good manners to be 5 to 10 minutes early for any appointment, but especially one as emotionally precarious as a first date. If you find yourself running late for any reason, notify your date ASAP, apologize, and keep them updated on your ETA. I know you’re not a jerk, so don’t act like one!

2. Dress well. Back in March, I wore a shirt with a hole in it on a first date. I’m not saying that’s why the relationship ended in bitterness and confusion, but I’m not not saying that, either. Look, I just think it’s a good omen to put effort into your appearance for a first date, both because it helps impress the other person and also because the spiffier you feel, the suaver you’ll behave. Your outfit should be setting-appropriate (probably don’t wear a church dress to a punk show, or a crop top to the symphony) and should make you feel badass and foxy. Bonus points if it includes at least one “conversation piece” (I like to wear my vulva ring on first dates, because, well, if someone’s not cool with that, there probably won’t be a second date).

3. Know what you want and be honest about it. Granted, not all first-date conversations meander to heavy topics like “What are you looking for?” or “Why did you decide to go on this date?” but if yours does, you should be prepared for that convo. If you’re only out for some casual fun, don’t tell your date you’re looking for something meaningful to pacify them; likewise, if you have your heart set on (eventual) commitment, don’t act like the Captain of Chill. It can be terrifying to frankly state what you want, but hey, dating is always a gamble. You’re far likelier to get what you crave if you’re able to ask for it. (And by the way: if you don’t know what you want at the moment, it’s okay to be honest about that, too.)

4. Have a solid pre-date ritual. This is crucial for me, as a person with anxiety. I need a Pavlovian get-pumped-up pre-date routine to banish anxiety and summon my best self. Mine involves loud, peppy music, lots of time spent on my makeup and hair, and texting with supportive friends. Get your prep on point and the rest of the evening will feel smoother for it.

5. Limit your substance intake. If you regularly partake of alcohol or drugs, I recommend you cool it on first dates. Even if your date matches you drink-for-drink, it probably won’t lead to good places: carrying on sharp conversations is harder when you’re blitzed, you don’t retain information as well, and you act different from how you normally would. If things get sexy, intoxicated consent is a fraught issue, especially with a new partner whose body and tastes you don’t know. Plus, if your date is someone from the internet or who you just don’t know very well, it’s safest to keep your wits about you, just incase. I know those soul-searching, three-beers-in conversations can be great fun – mulling over life’s big questions together while getting progressively flirtier – but maybe save those until you know this person a bit better, mmkay?

6. Pick a place where you can talk. In my experience, lots of folks get nervous about not seeming “cool” or “fun” enough to a new potential partner, so they’ll try to take you to some Mega-Awesome Thing like a stand-up comedy show or a drive-in movie theatre. It’s my staunch opinion that all first dates should be “let’s talk and get to know each other” dates. It’s best if this is a low-commitment situation like coffee or a drink – as opposed to a full meal, where you’re stuck in your seat for at least an hour even if the two of you end up hating each other. All my best first dates have involved going out for some kind of beverage together and talking for hours. If your conversation crackles and flows, that’s hugely useful information that you totally wouldn’t have found out if you’d met at a loud punk bar or arthouse cinema.

What I wore on a Tinder date in Minneapolis.

7. Be prepared for sex. Responsible adults know that dates might lead to sex and sex carries risks. If you’re going on dates without safer-sex supplies in your bag/pockets/car, what are you even doing?! In addition to condoms and whatnot, you should also prep your body and mind in whatever ways make you feel sex-ready – you don’t want to be in bed with your gorgeous new lover later tonight and find yourself unable to focus on anything but your prickly legs and musky junk.

8. …but don’t feel obligated to get sexy. There are all kinds of “rules” about sex on first dates. Some say it ruins a budding relationship; some say a sexless first date is a disastrous omen. The truth is, there are no set-in-stone timelines for how dates or relationships are “supposed” to go. If both people want to have sex and are emotionally and physically prepared to do so, there’s no reason why they shouldn’t – but there’s no rush, either. You do what feels right for you and don’t let anyone shame you. If your date is The Right Person, they’ll be on the same page as you about sex stuff – or they’ll be willing to get on the same page as you.

9. Ask them about them. My number-one complaint about most boys on Tinder is that they’re terrible conversationalists. Don’t be that guy. Be interested in your date, ask questions and then follow-up questions, and really listen to what they say. Strangers often seem boring until you discover what’s interesting about them. Give them the opportunity to show you that, by asking them about themselves. (This has the added effect of making you appear to be extremely charming and socially skilled. Yay!)

10. If it sucks, leave. Like Alana Massey says: “Stop wasting your time on bad first dates.” If someone is rude, or boring, or wants different things than you do, or you just don’t find them as attractive as you thought you would, you are not obligated to continue with the date. Be polite and respectful (if you can) when you duck out, but don’t let yourself be guilted into prolonging an encounter that’s absolutely not working for you. Those of us raised female (or Canadian) are especially prone to feigning enthusiasm for the sake of politeness, but you don’t have to do that. You deserve better than that.

What are your first-date commandments? What are some of the best and worst first dates you’ve been on?